Benzopyrone compounds, preparation method and use thereof

ABSTRACT

The invention relates to pesticide and bactericide, specifically to the benzopyrone compounds and its preparation method and use thereof. The benzopyrone compounds of the invention having general formula (I): The present invention, having good pesticide activity and broad bactericide activity, applied for controlling various pests in plants such as army worm, diamond backmoth and aphid, carmine spider mite, two-spotted spider mite, ladybeetle, mites and mosquito larvae. Various disease in plants can be controlled by the invention and that of grape downy mildew, rice sheath and culm blights rice blast, tomato early blight, tomato late blight wheat leaf rust, wheat leaf blotch, wheat powdery mildew, cucumber powdery mildew, cucumber downy mildew, cucumber grey mold and so on.

FIELD OF THE INVENTION

The invention relates to insecticides and fungicides, specifically tobenzopyrone compounds and its preparation method and use thereof.

BACKGROUND OF THE INVENTION

Benzopyrone and strobilurin (methoxyacrylate) compounds are naturalproducts and known with biological active. Compounds of the followinggeneral formula have ever been published in JP04-182461:

The structure of compound JP51 in JP04-182461 is as follows:

Biological active data of the compound in JP04-182461 have not beendisclosed. After synthesis and the biological evaluation, it was foundthat compound JP51 has low biological active.

SUMMARY OF THE INVENTION

The aim of the present invention is to provide benzopyrone compoundswith biological activity against all sorts of plant diseases and insectsat very low dosage, and the compounds can be applied in agriculture tocontrol diseases and insects in plant.

Detailed description of the invention is as follows:

The present invention offered benzopyrone compounds having generalformula (I):

wherein: A is selected from CH or N;

B is selected from O, S or NR₉; R₉ is selected from H or C₁-C₁₂alkyl;

R₁ and R₂ are respectively selected from H, C₁-C₁₂alkyl or C₁-C₁₂haloalkyl;

R₃ is selected from H, C₁-C₁₂alkyl, C₁-C₁₂ haloalkyl or C₁-C₁₂ alkoxy;

R₄, R₅, R₆, R₇, and R₈ may be the same or different, selected from H,halo, CN, NO₂, C₁-C₁₂alkyl, C₂-C₁₂alkenyl, C₂-C₁₂alkynyl,C₁-C₁₂haloalkyl, C₁-C₁₂alkoxy, C₁-C₁₂alkylthio, C₁-C₁₂alkylsulfonyl,C₁-C₁₂alkylcarbonyl, C₁-C₁₂alkoxyC₁-C₁₂alkyl, C₁-C₁₂alkoxycarbonyl,C₁-C₁₂alkoxycarbonyl C₁-C₁₂alkyl, C₁-C₁₂haloalkoxyC₁-C₁₂alkyl, or aminoC₁-C₁₂alkyl in which amino is substituted with 0-2 C₁-C₁₂ alkyl, 0-3substituted groups of aryl, aryloxyl, arylC₁-C₁₂alkyl, arylC₁-C₁₂alkoxy,aryloxyC₁-C₁₂alkyl, arylC₁-C₁₂alkoxylC₁-C₁₂alkyl, heteroaryl,heteroarylC₁-C₁₂alkyl, or heteroarylC₁-C₁₂alkoxyl, the 0-3 substitutedgroups may be selected from halo, NO₂, C₁-C₆alkyl, C₁-C₆haloalkyl,C₁-C₆alkoxy or C₁-C₆alkoxyC₁-C₆alkyl, and the groups having generalformula are as follows:

wherein: R₁₀ and R₁₁ are selected from H, C₁-C₁₂alkyl, aryl or arylC₁-C₁₂alkyl; when R₃, R₄, R₅, R₆, R₇, and R₈ are all H, B is not NR₉;and stereoisomer.

The preferred compounds of general formula (I) of this invention are:

A is selected from CH or N;

B is selected from O, S or NR₉; R₉ is selected from H or C₁-C₆alkyl;

R₁ and R₂ are respectively selected from H, C₁-C₆alkyl or C₁-C₆haloalkyl;

R₃ is selected from H, C₁-C₆alkyl, C₁-C₆ haloalkyl or C₁-C₆alkoxy;

R₄,R₅, R₆, R₇, and R₈ may be the same or different, selected from H,halo, CN, NO₂, C₁-C₆alkyl, C₂-C₆alkenyl, C₂-C₆alkynyl, C₁-C₆haloalkyl,C₁-C₆alkoxy, C₁-C₆ alkylthio, C₁-C₆alkylsulfonyl, C₁-C₆alkylcarbonyl,C₁-C₆ alkoxyC₁-C₆alkyl, C₁-C₆alkoxycarbonyl,C₁-C₆alkoxycarbonylC₁-C₆alkyl, C₁-C₆haloalkoxyC₁-C₆alkyl, or aminoC₁-C₆alkyl in which amino is substituted with 0-2 C₁-C₁₂ alkyl, 0-3substituted groups of aryl, aryloxyl, arylC₁-C₆alkyl, arylC₁-C₆alkoxy,aryloxyC₁-C₆alkyl, arylC₁-C₆alkoxylC₁-C₆alkyl, heteroaryl,heteroarylC₁-C₆alkyl, heteroarylC₁-C₆alkoxyl, the 0-3 substituted groupsmay be selected from halo, NO₂, C₁-C₂alkyl, C₁-C₂haloalkyl, C₁-C₂alkoxyor C₁-C₂alkoxyC₁-C₂alkyl, and groups having formula are as follows:

wherein: R₁₀ and R₁₁ are respectively selected from H, C₁-C₁₂alkyl, arylor arylC₁-C₆alkyl; when R₃, R₄,R₅, R₆, R₇, R₈ are all H, B is not NR₉;

Further more, the preferred compounds of general formula (I) of thisinvention are:

A is selected from CH or N;

B is selected from O or NH;

R₁ and R₂ are respectively selected from methyl;

R₃ is selected from H or methyl;

R₄, R₅, R₆, R₇, and R₈ may be the same or different, respectivelyselected from H, halo, CN, NO₂, C₁-C₆alkyl, C₂-C₆ alkenyl,C₁-C₆haloalkyl, C₁-C₆alkoxy, C₁-C₆alkylcarbonyl, C₁-C₆ alkoxyC₁-C₆alkyl,C₁-C₆alkoxycarbonyl, C₁-C₆alkoxycarbonylC₁-C₃alkyl,C₁-C₃haloalkoxyC₁-C₃alkyl, or amino C₁-C₃alkyl in which amino issubstituted with 0-2 C₁-C₃ alkyl, phenyl, phenoxy, phenylC₁-C₂alkyl,phenylC₁-C₂alkoxy, phenoxyC₁-C₂alkyl, phenylmethyl, phenylmethoxyl, orphenylmethoxyC₁-C₂alkyl substituted with 0-2 halo, NO₂, C₁-C₂alkyl,C₁-C₂haloalkyl, C₁-C₂alkoxy or C₁-C₂alkoxyC₁-C₂alkyl, and thesubstituted group having general formula is as follows:

wherein: R₁₀ and R₁₁ are respectively selected from H or C₁-C₆alkyl;when R₃, R₄, R₅, R₆, R₇, and R₈ are all H, B is not NH.

Even more preferred compounds of formula (I) of this invention are:

A is selected from CH or N;

B is selected from O or NH;

R₁ and R₂ are selected from methyl;

R₃ is selected from H or methyl;

R₄, R₅, R₆, R₇, and R₈ may be the same or different, respectivelyselected from H, Cl, Br, F, CN, C₁-C₆alkyl, C₁-C₆haloalkyl,C₁-C₆alkylcarbonyl, Cl -C₆alkoxy, C₁-C₆alkoxyC₁-C₃alkyl,C₁-C₃haloalkoxyC₁-C₃alkyl, amino C₁-C₃alkyl in which amino issubstituted with 0-2 C₁-C₃ alkyl, phenyl, phenoxy, phenylmethyl,phenylmethoxyl, substituted with 0-2 halo, NO₂, C₁-C₂alkyl,C₁-C₂haloalkyl, C₁-C₂alkoxy or C₁-C₂alkoxyC₁-C₂alkyl, and thesubstituted groups having general formula is as follows:

wherein: R₁₀ and R₁₁ are selected from methyl; when R₃, R₄, R₅, R₆, R₇,R₈ are all H, B is not NH.

The following is the meaning of terms in the general formula (I):

Halogen or halo is meant to include fluoro, chloro, bromo or iodo.

The alkyl includes either straight or branched chain alkyl such asmethyl, ethyl, propyl, isopropyl or tert-butyl.

The haloalkyl refers to straight or branched chain alkyl , in whichhydrogen atom may be all or partly substituted with halogen, such aschloromethyl, dichloromethyl, trichloromethyl, fluoromethyl,difluoromethyl, or trifluoromethyl.

The alkoxy refers to straight or branched chain alkyl, which is linkedto the structure by oxygen atom.

The haloalkoxy refers to straight or branched chain alkoxy, in whichhydrogen atom may be all or partly substituted with halogen_, such aschloromethoxy, dichloromethoxy, trichloromethoxy, fluoromethoxy,difluoromethoxy, trifluoromethoxy, chlorofluoromethoxy, ortrifluoroethoxy.

The alkenyl refers to an straight or branched, having double bonds atany position such as vinyl allyl. Substituted alkenyl includes arylvinylwhich is substituted at any position with any group.

The alkynyl refers to straight or branched, having triple bonds at anyposition. such as ethynyl, propynyl. Substituted alkynyl includesarylethynyl which is substituted at any position with any group.

The aryl and aryl in arylalkyl, arylalkenyl, arylalkynyl, aryloxy,aryloxyalkyl include phenyl and naphthyl.

The substituent group in phenyl, phenoxy, phenylmethyl, phenylmethoxyare H, alkyl, alkoxy, haloalkyl, haloalkoxy, halo, NO₂, CN and the like.The number of the substituent group can be from one to five.

The hetero aryl in this invention refers to five member ring or sixmember ring containing one or many N, O, S hetero atom such as furan,thiophene, pyrrole, pyrazole, imidazole, thiazole, triazole, pyridine,pyrimidine, pyrazine, pyridazine, triazine, quinoline, benzofuran.

Because of the C═C and C═N link to different substituted group, thecompounds of the invention may form geometrical isomer (the differentisomers are respectively expressed with Z and E). Z isomer and E isomerand their mixture in any proportion are included in the invention.

The present invention is explained by the compounds of the followingtable I, but without being restricted thereby.

Wherein R₁, R₂═CH₃;E is C(CH₃)═NOCH₃; M is C₆H₃-3, 4-(OCH₃)₂ TABLE 1Physical- No. A B R₃ R₄ R₅ R₆ R₇ R₈ property* 1 CH O H H H H H H oil 2CH O H H CH₃ H H H 140˜143 3 CH O H H CH₃ H H CH₃ 188-190 4 CH O H HC₆H₅ H H CH₃ 146-148 5 CH O H CH₃ CH₃ H H H 120˜122 6 CH O H CH₃ CH₃ H HCH₃ 174˜176 7 CH O H H CF₃ H H H 164˜166 8 CH O H H CH₃ H H E oil 9 CH OH H CH₃ H E H 183˜185 10 CH O H H CH₃ H COCH₃ H 169˜172 11 CH O H H CH₃H H COCH₃ 165˜167 12 CH O H Cl CH₃ H H H 162-164 13 CH O H H CH₂Cl H H H14 CH O H Cl CH₂Cl H H H 15 CH O H Cl CH₂OCH₃ H H H 16 CH O H Cl CH₂CH₃H H H 17 CH O H H CH₂CH₃ H H CH₃ 154-156 18 CH O H C₂H₅ CH₃ H H H132-135 19 CH O H H CH₂OCH₃ H H H 140-142 20 CH O H H CH₂OC₂H₅ H H H 21CH O H Cl CH₂OC₂H₅ H H H 22 CH O H OCH₃ CH₂OCH₃ H H H 23 CH O H N(CH₃)₂CH₃ H H H 24 CH O H CN H H H H 166-168 25 CH O H Cl CH₃ H H CH₃ 202-20426 CH O H H CH(CH₃)₂ H H H 128-130 27 CH O H C₃H₇ CH₃ H H H 142-144 28CH O H H tC₄H₉ H H H 29 CH O H H 4-Cl—C₆H₄ H H H 149-152 30 CH O H Cl4-Cl—C₆H₄ H H H 31 CH O H H 4-Cl—C₆H₄ H H CH₃ 32 CH O H Cl C₆H₅ H H H142-144 33 CH O H H CH₂CH₃ H H H 134-136 34 CH O H H CH₂C₂H₅ H H H118-120 35 CH O H H CH₂C₂H₅ H H CH₃ 146-148 36 CH O H Cl CH₂C₂H₅ H H H118-120 37 CH O H CH₃ CH₂C₂H₅ H H H 112-115 38 CH O H H 4-F—C₆H₄ H H H132-134 39 CH O H Cl 4-F—C₆H₄ H H H 40 CH O H H 4-F—C₆H₄ H H CH₃ 41 CH OH H 4-CF₃—C₆H₄ H H H 161-162 42 CH O H Cl 4-CF₃—C₆H₄ H H H 43 CH O H ClCH₂N(CH₃)₂ H H H 44 CH O H OCH₃ C₂H₅ H H H 45 CH O H OCH₃ CH₃ H H H 46CH O H OC₂H₅ CH₃ H H H 47 CH O H H CH₂OCH₂CF₃ H H H 48 CH O H ClCH₂OCH₂CF₃ H H H 49 CH O H F CF₃ H H H 50 CH O H F CH₃ H H H 163-164 51CH O H H CH₂N(CH₃)₂ H H H 52 CH O H H C₆H₅ H H H 130-133 53 CH O H Cl ClH H H 54 CH O H F Cl H H H 55 CH O H H CH₂OCH₂C₆H₅ H E H 56 CH O H OCH₃4-Cl—C₆H₅ H H H 57 CH O H F 4-Cl—C₆H₅ H H H 58 CH O H H M H H H 81-83 59CH O H Cl M H H H 60 CH O H Cl M H H CH₃ 61 CH O H CH₃S CH₃ H H H 62 CHO H CH₃SO₂ CH₃ H H H 63 CH O H F F H H H 64 CH O H CH₃SO₂ Cl H H H 65 CHO H H 4-NO₂—C₆H₅ H H H 66 CH O H Cl 4-NO₂—C₆H₅ H H H 67 CH O H H4-NO₂—C₆H₅ H H CH₃ 68 CH O H PhCH₂ CH₃ H H H 159-162 69 CH O H PhCH₂ CH₃H H CH₃ 70 CH O H CF₃CH₂O C₃H₇ H H H 71 CH NH H CH₃ CH₃ H H H 72 CH NH HCH₃ CH₃ H H CH₃ 73 CH NH H OCH₃ CF₃ CH₃ H H 74 CH NH H OCH₃ CH₃ F H E 75CH NH H H CF₃ H H CH₃ 76 CH NH H CH₃ CH₂Cl H H H 77 CH NH H CH₃ CH₂Cl HH CH₃ 78 CH NH H Cl CH₂Cl H H H 79 CH NH H H M Cl H E 80 CH NH H H M H HH 81 CH NH H H M H COCH₃ H 82 CH NH H H M H H COCH₃ 83 CH NH H ClCH₂OCH₃ H H H 84 CH NH H H 4-C₆H₅Cl H H H 85 CH NH H H 4-C₆H₅Cl H H CH₃86 CH NH H H CH₂OCH₃ H H CH₃ 87 CH NH H CH₃ CH₂OCH₃ H H H 88 CH NH H CH₃CH₂OCH₃ H H CH₃ 89 CH NH H H CH₂OCH₃ H H H 90 CH NH H H CH₂OCH₃ H H E 91CH NH H H CH₂OCH₂CF₃ H E H 92 CH NH H H CH₂N(CH₃)₂ H H H 93 CH NH H HCH₂OCH₂CF₃ H H COCH₃ 94 CH NH H Cl CH₂OC₂H₅ H H H 95 CH NH H H CH₂OC₂H₅H H H 96 CH NH H H CH₂OC₂H₅ H H CH₃ 97 CH NH H H CF₃ H H CH₃ 98 CH NH HCH₃ CF₃ H H H 99 CH NH H CH₃ Cl H H CH₃ 100 N O H Cl CH₃ H H H 172-174101 N O H H CH₃ H H H 150˜152 102 N O H H CH₃ H H CH₃ 178-180 103 N O HCH₃ CH₃ H H H 112˜118 104 N O H F CH₃ H H H 105 N O H H CF₃ H H Cl 106 NO H CH₃ CH₃ H H CH₃ 184˜186 107 N O H H CH₃ H E CO₂CH₃ 108 N O H H CH₃ HCOCH₃ CO₂CH₃ 109 N O H Cl CH₃ H H CH₃ 198-200 110 N O H H CH₂Cl H HCO₂CH₃ 111 N O H H H H H H 106˜110 112 N O H H CH₂Cl H H CF₃ 113 N O H H3-CF₃—C₆H₄ H H CF₃ 114 N O H CH₃ 3-CH₃—C₆H₄ H H CF₃ 115 N O H CH₃4-CH₃—C₆H₄ H H CF₃ 116 N O H H CH₂Cl H H H 117 N O H Cl CH₂Cl H H H 118N O H Cl CH₂F H H H 119 N O H H CH₂F H H H 120 N O H H CH₂Br H H H 121 NO H H CH₂OCH₃ H H CH₂N(CH₃)₂ 122 N O H Cl CH₂OCH₃ H H CH₂N(CH₃)₂ 123 N OH CH₃ CH₂OCH₃ H H CH₂N(CH₃)₂ 124 N O H H CH₂OCH₃ H H F 125 N O H CH₃CH₂OCH₃ H H F 126 N O H CH₃ CH₂OCH₃ H CO₂CH₃ CH₂N(CH₃)₂ 127 N O H HCH₂OCH₃ H H H 128 N O H H CH₂OCH₃ H H E 129 N O H H 3-CF₃—C₆H₄ H E H 130N O H H 3-CH₃—C₆H₄ H COCH₃ H 131 N O H H 4-CH₃—C₆H₄ H H COCH₃ 132 N O HCl CH₂OC₂H₅ H H H 133 N O H H CH₂OC₂H₅ H H H 134 N O H H CH₂OC₂H₅ H HCH₃ 135 N O H H 3-OCH₃—C₆H₄ H H CH₃ 136 N O H CH₃ 4-OCH₃—C₆H₄ H H H 137N O H CH₃ 2-OCH₃—C₆H₄ H H CH₃ 138 N O H H CH₂OC₂H₅ H H Cl 139 N O H HCH₂OC₂H₅ H H E 140 N O H H M H E H 141 N O H H 3-CF₃—C₆H₄ H COCH₃ H 142N O H H 3-CH₃—C₆H₄ H H COCH₃ 143 N O H H 4-CH₃—C₆H₄ H H H 144 N O H H2-Cl—C₆H₄ H H H 145 N O H H 3-Cl—C₆H₄ H H CH₃ 146 N O H H CH₂OCH₂CF₃ H HCH₃ 147 N O H CH₃ CH₂OCH₂CF₃ H H H 148 N O H CH₃ —CH₂OC₆H₅ H H CH₃ 149 NO H H —CH₂OC₆H₅ H H H 150 N O H H CH₂OCH₂C₆H₅ H H E 151 N O H HCH₂OCH₂C₆H₅ H H H 152 N O H H 4-Cl—C₆H₄ H COCH₃ H 153 N NH H H CH₃ H H H210-214 154 N NH H CH₃ CH₃ H H CH₃ 178˜180 155 N NH H H 2-Cl—C₆H₄ H HCH₃ 156 N NH H CH₃ 3-Cl—C₆H₄ H H H 157 N NH H CH₃ 4-Cl—C₆H₄ H H CH₃ 158N NH H Cl CH₂Cl H H H 159 N NH H Cl CH₃ H H H 160 N NH H H 3-CF₃—C₆H₄ HH H 161 N NH H H 3-CH₃—C₆H₄ H COCH₃ H 162 N NH H H 4-CH₃—C₆H₄ H H COCH₃163 N NH H H CH₂OCH₃ H H H 164 N NH H H 4-F—C₆H₄ H H H 165 N NH H H2-F—C₆H₄ H H CH₃ 166 N NH H H C₆H₃-3,5(Cl)₂ H H CH₃ 167 N NH H CH₃2-OCH₃—C₆H₄ H H H 168 N NH H CH₃ 2-OCH₃—C₆H₄ H H CH₃ 169 N NH H ClCH₂OCH₃ H H H 170 N NH H H CH₂OCH₃ H H E 171 N NH H H 3,5(Cl)₂—C₆H₃ H EH 172 N NH H H 2,4(Cl)₂—C₆H₃ H H H 173 N NH H H 3,4(Cl)₂—C₆H₃ H H H 174N NH H Cl CH₂OC₂H₅ H H H 175 N NH H H CH₂OC₂H₅ H H H 176 N NH H HCH₂OC₂H₅ H H CH₃ 177 N NH H H CF₃ H H CH₃ 178 N NH H CH₃ CF₃ H H H 179 NNH H CH₃ Cl H H CH₃ 180 N NH H H Cl H H H 181 N NH H H CH₃ H H Cl 182 NNH H H C₆H₅ H H Cl 183 N NH H CH₃ CH₃ H H F 184 N NH H CH₃ CH₃ H H H 185N NH H H CF₃ H H Cl 186 N NH H CH₃ 4-F—C₆H₄ H H CH₃ 187 N NH H H2-F—C₆H₄ H E CO₂CH₃ 188 N NH H H 2-Cl—C₆H₄ H COCH₃ CO₂CH₃ 189 N NH H H3-Cl—C₆H₄ H H CO₂CH₃ 190 N NH H H 4-Cl—C₆H₄ H H CO₂CH₃ 191 N NH H HCH₂Cl H CH₃ H 192 N NH H H CH₂Cl H CO₂C₂H₅ CF₃ 193 N NH H H CH₂Cl H HCF₃ 194 N NH H CH₃ M H CO₂C₂H₅ CF₃ 195 N NH H CH₃ CH₂Cl H H CF₃ 196 N NHH H CH₂Cl H H H 197 N NH H H CH₂Cl H H E 198 N NH H H CH₂Cl H E H 199 NNH H H CH₂Cl H COCH₃ H 200 N NH H CH₃ 3,5-diCl—C₆H₃ H CO₂CH₃ H 201 CH OCH₃ H H H H H 202 CH O CH₃ H CH₃ H H H 203 CH O CH₃ H CH₃ H H CH₃ 204 CHO CH₃ H C₆H₅ H H CH₃ 205 CH O CH₃ CH₃ CH₃ H H H 206 CH O CH₃ CH₃ CH₃ H HCH₃ 207 CH O CH₃ H CF₃ H H H 208 CH O CH₃ H CH₃ H H E 209 CH O CH₃ H CH₃H E H 210 CH O CH₃ H CH₃ H COCH₃ H 211 CH O CH₃ H CH₃ H H COCH₃ 212 CH OCH₃ H CH₂Cl H H H 213 CH O CH₃ Cl CH₂Cl H H H 214 CH O CH₃ H CH₂Cl H HCF₃ 215 CH O CH₃ H CH₂Cl H H CH₃ 216 CH O CH₃ CH₃ CH₂OCH₃ H H H 217 CH OCH₃ CH₃ CH₂OCH₃ H H CH₃ 218 CH O CH₃ OCH₃ CH₂Cl H H H 219 CH O CH₃ HCH₂Cl H H E 220 CH O CH₃ H CH₂Cl H E H 221 CH O CH₃ H CH₂Cl H COCH₃ H222 CH O CH₃ H CH₂Cl H H COCH3 223 CH O CH₃ H CH₂OCH₂CF₃ H H H 224 CH OCH₃ Cl CH₂OC₂H₅ H H H 225 CH O CH₃ Cl CH₂OCH₃ H H CH₃ 226 CH O CH₃ HCH₂OCH₃ H H CH₃ 227 CH O CH₃ CH₃ 3-CF₃—C₆H₄ H H H 228 CH O CH₃ CH₃3-CH₃—C₆H₄ H H CH₃ 229 CH O CH₃ H 4-CH₃—C₆H₄ H H H 230 CH O CH₃ H 2-Cl—C₆H₄ H H E 231 CH O CH₃ H 3-Cl —C₆H₄ H E H 232 CH O CH₃ H CF₃ H COCH₃ H233 CH O CH₃ Cl CH₂OCH₃ H H COCH₃ 234 CH O CH₃ OCH₃ CH₂OC₂H₅ H H H 235CH O CH₃ C₂H₅ CH₂OC₂H₅ H CH₃ H 236 CH O CH₃ H CH₂OC₂H₅ H H CH₃ 237 CH OCH₃ Cl CH₂OC₂H₅ H CO₂C₂H₅ CH₃ 238 CH O CH₃ CH₃ 2-F—C₆H₄ H H H 239 CH OCH₃ CH₃ 3-F—C₆H₄ H H CH₃ 240 CH O CH₃ H 4-F—C₆H₄ H H H 241 CH O CH₃ HCH₂OC₂H₅ H H E 242 CH O CH₃ H CH₂OC₂H₅ H E H 243 CH O CH₃ H CH₂OC₂H₅ HCOCH₃ H 244 CH O CH₃ H CH₂OC₂H₅ H H COCH₃ 245 CH O CH₃ H CH₂OCH₂CF₃ H HH 246 CH O CH₃ Cl CH₂OCH₂CF₃ H H H 247 CH O CH₃ H CF₃ H H CH₃ 248 CH OCH₃ H CH₂OCH₂CF₃ H H CH₃ 249 CH O CH₃ CH₃ CH₂OCH₂CF₃ H H H 250 CH O CH₃CH₃ —CH₂OPh H H CH₃ 251 CH O CH₃ H —CH₂OPh H H H 252 CH O CH₃ HCH₂OCH₂Ph H H E 253 CH O CH₃ H CH₂OCH₂Ph H E H 254 CH O CH₃ H 4-Cl—C₆H₅H COCH₃ H 255 CH O CH₃ H 4-Cl—C₆H₅ H H COCH₃ 256 CH O CH₃ H M H CO₂C₂H₅H 257 CH O CH₃ H M H H H 258 CH O CH₃ Cl M H H CH₃ 259 CH O CH₃ H M H HCH₃ 260 CH O CH₃ CH₃ M H H H 261 CH NH CH₃ Cl H H H H 262 CH NH CH₃ ClCH₃ H H H 263 CH NH CH₃ H CH₃ H H CH₃ 264 CH NH CH₃ H C₆H₅ H H CH₃ 265CH NH CH₃ CH₃ CH₃ H H H 266 CH NH CH₃ CH₃ CH₃ H H CH₃ 267 CH NH CH₃ OCH₃CF₃ H H H 268 CH NH CH₃ OCH₃ CH₃ H H E 269 CH NH CH₃ H CH₃ H E H 270 CHNH CH₃ H CH₃ H COCH₃ H 271 CH NH CH₃ H CH₃ H H COCH₃ 272 CH NH CH₃ HCH₂Cl H H H 273 CH NH CH₃ H M H H H 274 CH NH CH₃ H CH₂Cl H H CH₃ 275 CHNH CH₃ H CF₃ H H CH₃ 276 CH NH CH₃ CH₃ CH₂Cl H H H 277 CH NH CH₃ CH₃CH₂Cl H H CH₃ 278 CH NH CH₃ Cl CH₂Cl H H H 279 CH NH CH₃ H M H H E 280CH NH CH₃ H M H E H 281 CH NH CH₃ H M H COCH₃ H 282 CH NH CH₃ H M H HCOCH₃ 283 CH NH CH₃ Cl CH₂OCH₃ H H H 284 CH NH CH₃ H 4-C₆H₅Cl H H H 285CH NH CH₃ H 4-C₆H₅Cl H H CH₃ 286 CH NH CH₃ H CH₂OCH₃ H H CH₃ 287 CH NHCH₃ CH₃ CH₂OCH₃ H H H 288 CH NH CH₃ CH₃ CH₂OCH₃ H H CH₃ 289 CH NH CH₃ HCH₂OCH₃ H H H 290 CH NH CH₃ H CH₂OCH₃ H H E 291 CH NH CH₃ H CH₂OCH₂CF₃ HE H 292 CH NH CH₃ H CH₂OCH₂CF₃ H COCH₃ H 293 CH NH CH₃ H CH₂OCH₂CF₃ H HCOCH₃ 294 CH NH CH₃ Cl CH₂OC₂H₅ H H H 295 CH NH CH₃ H CH₂OC₂H₅ H H H 296CH NH CH₃ H CH₂OC₂H₅ H H CH₃ 297 CH NH CH₃ H CF₃ H H CH₃ 298 CH NH CH₃CH₃ CF₃ H H H 299 CH NH CH₃ CH₃ Cl H H CH₃ 300 CH NH CH₃ H Cl H H H 301N O CH₃ H CH₃ H H H 302 N O CH₃ H C₆H₅ H H Cl 303 N O CH₃ CH₃ CH₃ H H H304 N O CH₃ CH₃ CH₃ H H H 305 N O CH₃ H CF₃ H H Cl 306 N O CH₃ CH₃ CH₃ HH CH₃ 307 N O CH₃ H CH₃ H E CO₂CH₃ 308 N O CH₃ H CH₃ H COCH₃ CO₂CH₃ 309N O CH₃ H CH₃ H H CO₂CH₃ 310 N O CH₃ H CH₂Cl H H CO₂CH₃ 311 N O CH₃ H HH H H 312 N O CH₃ H CH₂Cl H H CF₃ 313 N O CH₃ H 3-CF₃—C₆H₄ H H CF₃ 314 NO CH₃ CH₃ 3-CH₃—C₆H₄ H H CF₃ 315 N O CH₃ CH₃ 4-CH₃—C₆H₄ H H CF₃ 316 N OCH₃ H CH₂Cl H H H 317 N O CH₃ H CH₂Cl H H E 318 N O CH₃ H CH₂Cl H E H319 N O CH₃ H CH₂Cl H COCH₃ H 320 N O CH₃ H CH₂Cl H H COCH3 321 N O CH₃H CH₂OCH₃ H H CH₂N(CH₃)₂ 322 N O CH₃ Cl CH₂OCH₃ H H CH₂N(CH₃)₂ 323 N OCH₃ CH₃ CH₂OCH₃ H H CH₂N(CH₃)₂ 324 N O CH₃ H CH₂OCH₃ H H F 325 N O CH₃CH₃ CH₂OCH₃ H H F 326 N O CH₃ CH₃ CH₂OCH₃ H CO₂CH₃ CH₂N(CH₃)₂ 327 N OCH₃ H CH₂OCH₃ H H H 328 N O CH₃ H CH₂OCH₃ H H E 329 N O CH₃ H 3-CF₃—C₆H₄H E H 330 N O CH₃ H 3-CH₃—C₆H₄ H COCH₃ H 331 N O CH₃ H 4-CH₃—C₆H₄ H HCOCH₃ 332 N O CH₃ Cl CH₂OC₂H₅ H H H 333 N O CH₃ H CH₂OC₂H₅ H H H 334 N OCH₃ H CH₂OC₂H₅ H H CH₃ 335 N O CH₃ H 3-OCH₃—C₆H₄ H H CH₃ 336 N O CH₃ CH₃4-OCH₃—C₆H₄ H H H 337 N O CH₃ CH₃ 2-OCH₃—C₆H₄ H H CH₃ 338 N O CH₃ HCH₂OC₂H₅ H H Cl 339 N O CH₃ H CH₂OC₂H₅ H H E 340 N O CH₃ H M H E H 341 NO CH₃ H 3-CF₃—C₆H₄ H COCH₃ H 342 N O CH₃ H 3-CH₃—C₆H₄ H H COCH₃ 343 N OCH₃ H 4-CH₃—C₆H₄ H H H 344 N O CH₃ H 2-Cl—C₆H₄ H H H 345 N O CH₃ H3-Cl—C₆H₄ H H CH₃ 346 N O CH₃ H CH₂OCH₂CF₃ H H CH₃ 347 N O CH₃ CH₃CH₂OCH₂CF₃ H H H 348 N O CH₃ CH₃ —CH₂OPh H H CH₃ 349 N O CH₃ H —CH₂OPh HH H 350 N O CH₃ H CH₂OCH₂Ph H H E 351 N O CH₃ H CH₂OCH₂Ph H E H 352 N OCH₃ H 4-Cl—C₆H₄ H COCH₃ H 353 N NH CH₃ H CH₃ H H H 354 N NH CH₃ CH₃ CH₃H H CH₃ 355 N NH CH₃ H 2-Cl—C₆H₄ H H CH₃ 356 N NH CH₃ CH₃ 3-Cl—C₆H₄ H HH 357 N NH CH₃ CH₃ 4-Cl—C₆H₄ H H CH₃ 358 N NH CH₃ H CH₂Cl H H H 359 N NHCH₃ H M H H E 360 N NH CH₃ H 3-CF₃—C₆H₄ H E H 361 N NH CH₃ H 3-CH₃—C₆H₄H COCH₃ H 362 N NH CH₃ H 4-CH₃—C₆H₄ H H COCH₃ 363 N NH CH₃ H CH₂OCH₃ H HH 364 N NH CH₃ H 4-F—C₆H₄ H H H 365 N NH CH₃ H 2-F—C₆H₄ H H CH₃ 366 N NHCH₃ H C₆H₃-3,5(Cl)₂ H H CH₃ 367 N NH CH₃ CH₃ 2-OCH₃—C₆H₄ H H H 368 N NHCH₃ CH₃ 2-OCH₃—C₆H₄ H H CH₃ 369 N NH CH₃ Cl CH₂OCH₃ H H H 370 N NH CH₃ HCH₂OCH₃ H H E 371 N NH CH₃ H C₆H₃-3,5(Cl)₂ H E H 372 N NH CH₃ HCH₂OCH₂CF₃ H COCH₃ H 373 N NH CH₃ H CH₂OCH₂CF₃ H H COCH₃ 374 N NH CH₃ ClCH₂OC₂H₅ H H H 375 N NH CH₃ H CH₂OC₂H₅ H H H 376 N NH CH₃ H CH₂OC₂H₅ H HCH₃ 377 N NH CH₃ H CF₃ H H CH₃ 378 N NH CH₃ CH₃ CF₃ H H H 379 N NH CH₃CH₃ Cl H H CH₃ 380 N NH CH₃ H Cl H H H 381 N NH CH₃ H CH₃ H H Cl 382 NNH CH₃ H C₆H₅ H H Cl 383 N NH CH₃ CH₃ CH₃ H H F 384 N NH CH₃ CH₃ CH₃ H HH 385 N NH CH₃ H CF₃ H H Cl 386 N NH CH₃ CH₃ 4-F—C₆H₄ H H CH₃ 387 N NHCH₃ H 2-F—C₆H₄ H E CO₂CH₃ 388 N NH CH₃ H 2-Cl—C₆H₄ H COCH₃ CO₂CH₃ 389 NNH CH₃ H 3-Cl—C₆H₄ H H CO₂CH₃ 390 N NH CH₃ H 4-Cl—C₆H₄ H H CO₂CH₃ 391 NNH CH₃ H CH₂Cl H CH₃ H 392 N NH CH₃ H CH₂Cl H CO₂C₂H₅ CF₃ 393 N NH CH₃ HCH₂Cl H H CF₃ 394 N NH CH₃ CH₃ M H CO₂C₂H₅ CF₃ 395 N NH CH₃ CH₃ CH₂Cl HH CF₃ 396 N NH CH₃ H CH₂Cl H H H 397 N NH CH₃ H CH₂Cl H H E 398 N NH CH₃H CH₂Cl H E H 399 N NH CH₃ H CH₂Cl H COCH₃ H 400 N NH CH₃ CH₃3,5-diCl—C₆H₃ H CO₂CH₃ H 401 CH O H C₃H₇i CH₃ H H H oil 402 CH O Hn-C₄H₉ CH₃ H H H 117-118 403 CH O H n-C₅H₁₁ CH₃ H H H 404 CH O H C₂H₄PriCH₃ H H H oil 405 CH O H n-C₆H₁₃ CH₃ H H H 113-115 406 CH O H H n-C₄H₉ HH H 407 CH O H H n-C₅H₁₁ H H H 408 CH O H H CH(CH₃)₂ H H CH₃ 110-112 409CH O H n-C₃H₇ n-C₃H₇ H H H 112-114 410 N O H Cl n-C₃H₇ H H H 136-138 411N O H Cl C₆H₅ H H H 166-168 412 N O H n-C₃H₇ CH₃ H H H 121-122 413 N O Hn-C₄H₉ CH₃ H H H 100-102 414 N O H n-C₆H₁₃ CH₃ H H H 75-78 415 CH O HCH₃ n-C₄H₉ H H H 416 CH O H C₂H₅ n-C₄H₉ H H H 417 CH O H C₃H₇ n-C₄H₉ H HH 418 CH O H i-C₃H₇ n-C₄H₉ H H H 419 CH O H n-C₄H₉ n-C₄H₉ H H H 420 CH OH CH₃ n-C₅H₁₁ H H H 421 CH O H C₂H₅ n-C₅H₁₁ H H H 422 CH O H C₃H₇n-C₅H₁₁ H H H 423 CH O H i-C₃H₇ n-C₅H₁₁ H H H 424 CH O H n-C₄H₉ n-C₅H₁₁H H H 425 CH O H H n-C₆H₁₃ H H H 426 CH O H CH₃ n-C₆H₁₃ H H H 427 CH O HC₂H₅ n-C₆H₁₃ H H H 428 CH O H C₃H₇ n-C₆H₁₃ H H H 429 CH O H i-C₃H₇n-C₆H₁₃ H H H 430 CH O H n-C₄H₉ n-C₆H₁₃ H H H 431 N O H CH₃ n-C₄H₉ H H H432 N O H C₂H₅ n-C₄H₉ H H H 433 N O H C₃H₇ n-C₄H₉ H H H 434 N O H i-C₃H₇n-C₄H₉ H H H 435 N O H n-C₄H₉ n-C₄H₉ H H H 436 N O H CH₃ n-C₅H₁₁ H H H437 N O H C₂H₅ n-C₅H₁₁ H H H 438 N O H C₃H₇ n-C₅H₁₁ H H H 439 N O Hi-C₃H₇ n-C₅H₁₁ H H H 440 N O H n-C₄H₉ n-C₅H₁₁ H H H 441 N O H H n-C₆H₁₃H H H 442 N O H CH₃ n-C₆H₁₃ H H H 443 N O H C₂H₅ n-C₆H₁₃ H H H 444 N O HC₃H₇ n-C₆H₁₃ H H H 445 N O H i-C₃H₇ n-C₆H₁₃ H H H 446 N O H n-C₄H₉n-C₆H₁₃ H H H 447 N NH H CH₃ n-C₄H₉ H H H 448 N NH H C₂H₅ n-C₄H₉ H H H449 N NH H C₃H₇ n-C₄H₉ H H H 450 N NH H i-C₃H₇ n-C₄H₉ H H H 451 N NH Hn-C₄H₉ n-C₄H₉ H H H 452 N NH H CH₃ n-C₅H₁₁ H H H 453 N NH H C₂H₅ n-C₅H₁₁H H H 454 N NH H C₃H₇ n-C₅H₁₁ H H H 455 N NH H i-C₃H₇ n-C₅H₁₁ H H H 456N NH H n-C₄H₉ n-C₅H₁₁ H H H 457 N NH H H n-C₆H₁₃ H H H 458 N NH H CH₃n-C₆H₁₃ H H H 459 N NH H C₂H₅ n-C₆H₁₃ H H H 460 N NH H C₃H₇ n-C₆H₁₃ H HH 461 N NH H i-C₃H₇ n-C₆H₁₃ H H H 462 N NH H n-C₄H₉ n-C₆H₁₃ H H H 463 CHO H H CH₂-Ph-4-Cl H H H 464 CH O H CH₃ CH₂-Ph-4-Cl H H H 465 CH O H C₂H₅CH₂-Ph-4-Cl H H H 466 CH O H CH₂-Ph-4-Cl CH₃ H H H 467 CH O HCH₂-Ph-4-Cl C₂H₅ H H H 468 CH O H CH₂-Ph-4-Cl C₃H₇ H H H 469 CH O H CH₃CF₃ H H H 470 CH O H Cl CF₃ H H H 471 CH O H C₂H₅ CF₃ H H H 472 CH O Hn-C₃H₇ CF₃ H H H 473 CH O H n-C₄H₉ CF₃ H H H 474 CH O H H CH₂CH₂-Ph- H HH 4-Cl 475 CH O H CH₃ H H H 476 CH O H H CH₂Bu-t H H H 477 CH O H CH₃CH₂Bu-t H H H 478 CH O H n-C₃H₇ CH₂Bu-t H H H 479 CH O H CH₂Bu-t CH₃ H HH 480 CH O H CH₂CH₂-Ph- CH₃ H H H 4-Cl 481 CH O H C₂H₅ H H H 482 CH O HC₃H₇ H H H 483 CH O H CO₂CH₃ CH₃ H H H 484 CH O H CO₂CH₃ CF₃ H H H 485CH O H CO₂C₂H₅ C₂H₅ H H H 486 CH O H CO₂C₂H₅ n-C₃H₇ H H H 487 CH O HCONHCH₃ CH₃ H H H 488 CH O H CONHC₂H₅ CH₃ H H H 489 CH O H CON(CH₃)₂ CH₃H H H 490 CH O H CH₃ CO₂CH₃ H H H*stands for melting point. ° C. is the unit.

The present invention also includes preparation of benzopyrone compoundsand their isomers having general formula (I).

The compounds of formula I can be easily prepared by reaction of thebenzylhalide having general formula (II) with benzopyrone compoundscontaining hydroxy group having general formula (III) under basecondition according to the scheme I.

wherein: Z is leaving group, such as halogen (Cl, Br, or I).

R₁, R₂, R₃, R₄, R₅, R₆, R₇, R₈, A, B, is as defined above.

Preparation condition of compounds having general formula (I): In propersolvent, hydroxylbenzopyrone compounds having general formula (III) aretreated with proper base to become salts, then the compound havinggeneral formula (II) is added into the mixture, the reaction is carriedout at proper temperature. After reaction is completed, the targetcompound I is obtained by normal way.

The proper solvent mentioned may be selected from the following ones,such as tetrahydrofuran, acetonitrile, toluene, xylene, benzene, DMF,DMSO, acetone or butanone and so on.

The proper base mentioned may be selected from the following ones, suchas potassium hydroxide, sodium hydroxide, potassium carbonate, sodiumcarbonate, sodium bicarbonate, triethylamine, pyridine, pyridine orsodium hydride and so on.

The proper temperature mentioned is from room temperature to boilingpoint of solvent. Normal temperature is from 20 to 100° C.

The reaction may be finished in the course of 30 minutes-20 hours,generally 1-10 hours.

The reaction can be controlled by Thin-Layer Chromatography.

The intermediates of general formula (II) can be prepared according tothe known methods refer to U.S. Pat. No. 4,723,034 and U.S. Pat. No.5,554,578.

Some of the hydroxylbenzopyrone compounds having general formula (III)are available from the chemical company, and are also prepared accordingto the methods reported in Journal of Medicinal Chemistry, 2001, 44(5),664-671, by the reaction R₅COCHR₄CO₂CH₃(C₂H₅) with substitutedresorcinol. Moreover, the compound may be straightly used to prepare thetarget compounds without further purification. Some of thehydroxylbnezopyrone compounds having general formula (HI) synthesizedare showed in table 2. TABLE 2 III R₄ R₅ R₆ R₇ R₈ Physical property*III-1 H CH₃ H H COCH₃ 158-160 III-2 H CH₃ H H C(═NOMe)CH₃ 129-140 III-3H H₃ H H CO₂CH₃ 219-222 III-4 H CH₃ H H CH₃ 256-258 III-5 Cl CH₃ H H H230-234 III-6 H CF₃ H H H 180-183 III-7 C₆H₅CH₂ CH₃ H H H 208-212 III-8H 4-F—C₆H₄ H H H 256-262 III-9 H 3,4-(MeO)₂C₆H₄ H H H 184-188 III-10 FCH₃ H H H 203-206 III-11 H C₆H₅ H H H 240-242 III-12 H C₆H₅ H H CH₃260-262 III-13 Cl C₆H₅ H H H 188-190 III-14 CH₃ CH₃ H H H 118-120 III-15CH₃ CH₃ H H CH₃ 218-222 III-16 H n-C₃H₇ H H CH₃ 176-178 III-17 Cl n-C₃H₇H H H 148-150 III-18 H i-C₃H₇ H H H 160-162 III-19 n-C₆H₁₃ CH₃ H H H170-172 III-20 i-C₃H₇CH₂CH₂ CH₃ H H H 101-102 III-21 n-C₄H₉ CH₃ H H H134-136 III-22 n-C₃H₇ CH₃ H H H 142-144 III-23 H CH₂OCH₃ H H H 186-190*stands for melting point. ° C. is the unit.

The compounds of general formula (V) and (VII) can be easily prepared byreaction of the general formula (IV) and (VI), respectively, withmethylamine aqueous solution.

The present invention also provides a composition of insecticides andfungicides. The active ingredients of the composition are the compoundshaving general formula (I), wherein the active ones being present in atotal amount of 0.1 to 99% by weight, the rest being the acceptablecarrier by agriculture.

The present invention, further more, provides preparation method of thesaid composition thereon. The compounds of general formula (I) and thecarrier are mixed. The said composition may be a single componentcompound or mixture of compounds with several components.

The carrier in the invention accords to the requirements: it is easy toapply to the sites being to be treated for the carrier after it isconfected with active component. For example, the sites could be plant,seed or soil convenient for store, transport or operation. The carriercould be solid or liquid, including the liquid which usually turns fromgas condition under pressure. And the carriers which are used to confectinsecticidal, bactericidal composition are applied.

Suitable solid carriers include natural and synthetic clays andsilicates, for example diatomaceous earths, talcs, magnesium aluminiumsilicates, aluminium silicates(kaolin), montmorillonites and micas;calcium carbonate; calcium sulphate; ammonium sulphate; syntheticsilicon oxides and synthetic calcium silicates or aluminium silicates;elements, for example carbon and sulphur; natural and synthetic resins,for example coumarone resins, polyvinyl chloride, and styrene polymersor copolymers; solid polychlorophenols; bitumen; waxes, beeswax orparaffin wax for instance.

Suitable liquid carriers include water, alcohols such as isopropanol oralcohol; ketones such as acetone, methyl ethyl ketone, methyl isopropyketone or cyclohexanone; ethers; aromatics such as benzene, xylene,toluene; petroleum fractions such as kerosene or mineral oils,chlorinated aliphatic hydrocarbons such as carbon tetrachloride,tetrachloride ethylene or trichloride ethylene. Mixtures of thesedifferent liquids generally are often suitable.

The compositions of insecticides and fungicides are often formulated andtransported in a concentrated form which is subsequently diluted by theuser before application. The presence of small amounts of surfactantfacilitates this process of dilution. Thus preferably at least onecarrier in a composition according to the invention is a surfactant. Forexample the composition may contain at least two carriers, at least oneof which is, a surfactant.

A surfactant may be an emulsifier, a dispersant or a wetting agent; itmay be nonionic or ionic. Examples of suitable surfactant include thesodium or calcium salts of polyacrylic acids and lignin sulphonic acids;the condensation products of fatty acids or aliphatic amines or amidescontaining at least 12 carbon atoms in the molecule with ethylene oxideand/or propylene oxide; fatty acid esters of glycol, sorbic alcohol,sucrose or pentaerythritol and condensations of these with ethyleneoxide and/or propylene oxide; condensation products of fatty alcohol oralkyl phenols such as p-octylphenol or p-octylcresol, withethylene-oxide and/or propylene oxide; sulphates or sulphonates of thesecondensation products; alkaline metal salts or alkaline earth metalsalts, preferably sodium salts, of sulphuric or sulphonic acid esterscontaining at least 10 carbon atoms in the molecule, for example sodiumlauryl sulphate, sodium secondary alkyl sulphates, sodium salts ofsulphonated castor oil, and sodium alkylaryl sulphonates such as sodiumdodecylbenzene sulphonate.

Examples of compositions and formulations according to the invention arewettable powder, Dustable powder, granule and aqueous solution;emulsifiable concentrate, emulsion, suspension concentrate, aerosolcomposition and fumigant. Wettable powder usually contains 25, 50 or 75%weight(ab.w) of active ingredient and usually contain in addition tosolid inert carrier, 3-10% w of a dispersant and, where necessary, 0-10%w of stabiliser(s) and/or other additives such as penetrants orstickers. Dustable powder are usually formulated as a dust concentratehaving a similar composition to that of a wettable powder but adispersant, and are diluted with further solid carrier to give acomposition usually containing 0.5-10% weight of active ingredient.Granules are usually prepared to have a size between 10 and 100 BS mesh(1.676-0.152 mm), and may be manufactured by agglomeration orimpregnation techniques. Generally, granules contain 0.5-75% w activeingredient and 0-10% weight of additives such as stabilisers,surfactants, slow release modifiers. The so-called “dry flowablepowders” consist of relatively small granules having a relatively highconcentration of active ingredient. Emulsifiable concentrates usuallycontain, in addition to a solvent and, when necessary, co-solvent, 1-50%weight /volume(ab. w/v) active ingredient, 2-20% w/v emulsifiers and0-20% w/v of other additives such as stabilisers, penetrants andcorrosion inhibitors. Suspension concentrates are usually contain 10-75%w active ingredient, 0.5-15% w of dispersing agents, 0.1-10% w of otheradditives such as defoamers, corrosion inhibitors, stabilisers,penetrants and stickers.

Aqueous dispersant and emulsions, for example compositions obtained bydiluting a wettable powder or a concentrate according to the inventionwith water, also lie within the scope of the invention. The saidemulsions may be of the water-in-oil or of the oil-in-water type.

The composition to which one or more other fungicides are added haswider spectrum activity than single compound having general formula (I).In addition, other fungicides may have synergistic effect on thefungicidal activity of the compound having general formula (I). Thecompound having general formula (I) can also be used with otherinsecticides, or with another fungicide and other insecticidessimultaneously.

This invention has the following advantages:

The compounds of present invention have very good insecticide activity,and may be used to control insects such as armyworm, diamond backmoth,aphids, carmine spider mite, two-spotted spider mite, lady beetles,mites and culex mosquitoes, especially for lady beetles and culexmosquitoes. All these attributes are suitable for integrated insectmanagement.

The compounds of present invention have wide spectrum fungicidalactivity, and may be used to control diseases in all sorts of plantscaused by by oomycete, basidiomycete, ascomycete pathogens, and it mayalso provide good control efficacy at very low rate because of the highactivity. These compounds have penetration activity and can be used assoil and foliar fungicides. They can provide satisfied control of grapedowny mildew, rice sheath blight, rice blast, tomato early blight,tomato late blight, wheat leaf rust, wheat leaf blotch, wheat powderymildew, cucumber powdery mildew, cucumber downy mildew and cucumber greymold

DESCRIPTION OF THE INVENTION IN DETAIL

The following examples are illustrative of the present invention.

PREPARATION EXAMPLE Example 1 the Preparation of Compound 1

A reaction flask was charged a suspension of 60% sodium hydride 0.84 g(washed with petroleum ether), and then 30 ml of dryN,N-dimethylformamide (DMF) was added, the mixture was stirred at roomtemperature for 30 minutes. To this agitated suspension, 1.7 g of7-hydroxycoumarin was added, the mixture was agitated continuously tillto no gas emerging. 3.0 g of methyl(E)-α-[2-(bromomethyl)phenyl]-β-methoxyacrylate was added to thereaction mixture and they were agitated continuously for 3 hours at roomtemperature. The reaction mixture was poured into ice water, extractedwith ethyl acetate 3 times. The combined extracts were washed with brine3 times, dried, filtered and concentrated under vacuum, to obtain thecrude oil product 5 g. This was subjected to column chromatography toobtain 2.8 g of compound 1 as a faint red-yellow oily substance in 76.5%yield.

¹HNMR(300 MHz, internal standard=TMS, CDCl₃): δppm 3.69(3H, s), 3.88(3H,s), 5.04(2H, s), 6.19-6.23(1H, d), 6.77(1H, s), 6.83-6.87(1H, d),7.18-7.20(1H, m), 7.26-7.34(4H, m), 7.48-7.64(2H, m).

Example 2 the Preparation of Compound 2

A reaction flask was charged a suspension of 60% sodium hydride 0.45 g(washed with petroleum ether), and then 20 ml of dryN,N-dimethylformamide (DMF) was added, the mixture was stirred at roomtemperature for 30 minutes. To this agitated suspension, 1.0 g of7-hydroxy-4-methylcoumarin was added, the mixture was agitatedcontinuously till to no gas emerging. 1.66 g of methyl(E)-α-[2-(chloromethyl)phenyl]-β-methoxyacrylate was added to thereaction mixture and they were agitated continuously for 3 hours at roomtemperature. The reaction mixture was poured into ice water, extractedwith ethyl acetate 3 times. The combined extracts were washed with brine3 times. Dried, filtered and concentrated, to obtain the crude product,as a yellow solid substance. This was subjected to columnchromatography, using a 1:2 mixture of ethyl acetate and petroleum etheras the eluting solution to obtain 1.73 g of compound 2, with meltingpoint of 140-143° C. in 80% yield.

¹HNMR(300 MHz, internal standard=TMS, CDCl₃): δppm 2.38(3H, s), 3.74(3H,s), 3.89(3H, s), 5.04(2H, s), 6.11 (1H, s), 6.77(1H, s), 6.85-6.89(1H,d), 7.17-7.20(1H, m), 7.32-7.35(2H, m), 7.49-7.52(2H, m), 7.64(1H, s).

Example 3 the Preparation of Compound 101

A reaction flask was added 1.2 g of K₂CO₃, 1.0 g of7-hydroxy-4-methylcoumarin, 1.70 g of methyl(E)-2-(bromomethyl)-α-(methoxyimino)benzeneacetate and 20 ml Butanone,the reaction mixture was refluxed and agitated continuously for 5 hours.The reaction mixture was poured into ice water, extracted with ethylacetate 3 times. The combined extracts were washed with brine 3 times,dried, filtered and concentrated under vacuum, to obtain the crudeproduct, as a yellow solid substance. This was subjected to columnchromatography, using a 1:2 mixture of ethyl acetate and petroleum etheras the eluting solution to obtain 1.77 g of compound 101, with meltingpoint of 150-152° C. in 83% yield.

¹HNMR(300 MHz, internal standard=TMS, CDCl₃): δppm 2.39(3H, s), 3.87(3H,s), 4.05(3H, s), 5.02(2H, s), 6.13(1H, s), 6.80-6.86(2H, m),7.23-7.26(1H, m), 7.43-7.49(4H, m).

Example 4 the Preparation of Compound 153

A reaction flask was added 0.27 g of compound 101, more than twofold(mol)methylamine and 30 ml methanol, the reaction mixture wascontinuously agitated overnight, then concentrated and extracted withethyl acetate 2 times. The combined extracts were washed with water 3times and then washed with brine 2 times, dried, filtered andconcentrated, to obtain 0.24 g of compound 153, with melting point of210-214° C. in 89% yield.

¹HNMR(300 MHz, internal standard=TMS, CDCl₃): δppm 2.38(3H, s),2.91-2.93(3H, d), 3.97(3H, s), 5.02(2H, s), 6.13(1H, s), 6.82-6.87(3H,m), 7.23(1H, d), 7.39-7.50(4H, m).

The preparation of other compounds, please refers to the way as above.¹HNMR of other compounds are provided as follows (300 MHz, internalstandard=TMS, CDCl₃):

Compound 3: δppm 2.36(3H, s), 2.37(3H, s), 3.72(3H, s), 3.84(3H, s),5.09(2H, s), 6.13 (1H, s), 6.75-6.78(1H, d), 7.18-7.21(1H, m),7.34-7.36(3H, m), 7.50-7.52(1H, m)7.61(1H, s).

Compound 4: δppm 2.41(3H, s), 3.69(3H, s), 3.81(3H, s), 5.08(2H, s),6.20(1H, s), 6.68-6.71(1H, d), 7.18-7.21(4H, m), 7.32-7.50(5H, m),7.59(1H, s), 7.92(1H, m).

Compound 5: δppm 2.17(3H, s), 2.35(3H, s), 3.73(3H, s), 3.88(3H, s),5.02(2H, s), 6.78(1H, s), 6.83-6.85(1H, d), 7.31-7.34(3H, m),7.45-7.47(2H, d), 7.62(1H, s).

Compound 6: δppm 2.32(3H, s), 2.31-2.36(6H, d), 3.69(3H, s), 3.84(3H,s), 5.07(2H, s), 6.74-6.77(1H, d), 7.17-7.20(1H, m), 7.31-7.36(3H, m),7.51-7.54(1H, m), 7.61(1H, s).

Compound 12: δppm 2.53(3H, s), 3.74(3H, s), 3.89(3H, s), 5.04(2H, s),6.78(1H, s), 6.83-6.85(1H, d), 7.18-7.21(1H, m), 7.32-7.35(2H, m),7.47-7.50(2H, d), 7.64(1H, s).

Compound 17: δppm 1.25-1.32(3H, m), 2.36(3H, s), 2.74-2.76(2H, m),3.71(3H, s), 3.84(3H, s), 5.08(2H, s), 6.15(1H, s), 6.75-6.78(1H, d),7.18-7.21(1H, m), 7.33-7.38(3H, m), 7.50-7.54(1H, m), 7.61(1H, s).

Compound 18: δppm 1.10-1.15(3H, t), 2.37(3H, s), 2.60-2.68(2H, q),3.74(3H, s), 3.89(3H, s), 5.03(2H, s), 6.76 (1H, d), 6.84-6.88(1H, dd),7.18-7.21(1H, m), 7.32-7.35(2H, m), 7.45-7.53(2H, m), 7.63(1H, s).

Compound 19: δppm 3.48(3H, s), 3.74(3H, s), 3.89(3H, s), 4.56(2H, s),5.04(2H, s), 6.34(1H, s), 6.79(1H, d), 6.84-6.88(1H, dd), 7.18-7.21(1H,m), 7.30-7.36(2H, m), 7.41-7.44(1H, d), 7.48-7.51 (1H, m), 7.64(1H, s).

Compound 24: δppm 3.72(3H, s), 3.92(3H, s), 5.10(2H, s), 6.78(1H, s),6.94-7.21(1H, d), 7.22(1H, m), 7.33-7.35(2H, m), 7.36-7.45(2H, m),7.66(1H, s), 8.13(1H, s).

Compound 25: δppm 2.36(3H, d), 2.62(3H, d), 3.71(3H, s), 3.84(3H, s),5.09(2H, s), 6.82(1H, d), 7.19-7.21(1H, m), 7.33-7.35(3H, m),7.36-7.37(1H, m), 7.61(1H, s).

Compound 26: δppm 1.25-1.30(6H, m), 3.20-3.23(1H, m), 3.74(3H, s),3.91(3H, s), 5.04(2H, s), 6.15(1H, s), 6.790-6.799(1H, d), 6.80-6.90(1H,m), 7.18-7.23(1H, m), 7.32-7.37(2H, m), 7.48-7.57(2H, m), 7.64(1H, s).

Compound 27: 8ppm 0.95-1.00(3H, t), 1.58(2H, m), 2.36(3H, s), 2.58(2H,t), 3.73(3H, s), 3.89(3H, s), 5.02(2H, s), 6.75(1H, d), 6.84-6.88(1H,dd), -7.18(1H, m), 7.31-7.34(1H, m), 7.47-7.51(2H, m), 7.63(1H, s).

Compound 29: δppm 3.74(3H, s), 3.90(3H, s), 5.06(2H, s, ), 6.17(1H, s),6.80-6.85 (2H, m), 7.24-7.26(1H, m), 7.28-7.35(5H, m), 7.38-7.51(3H, m),7.66(1H, s).

Compound 32: δppm 3.73(3H, s), 3.90(3H, s), 5.05(2H, s), 6.75-6.78 (1H,dd), 6.84-6.85(1H, d), 6.94-6.98(1H, d), 7.19-7.21(1H, m), 7.30-7.35(4H,m), 7.53-7.55(4H, m), 7.65(1H, s).

Compound 33: δppm 1.27-1.32(3H, m), 2.74-2.77(2H, m), 3.74(3H, s),3.89(3H, s), 5.04(2H, s), 6.13(1H, s), 6.78-6.79(1H, d), 6.85-6.89(1H,m), 7.18-7.21(1H, m), 7.32-7.35(2H, m), 7.48-7.52(2H, m), 7.64(1H, s).

Compound 34: δppm 0.90-1.03(3H, m), 1.67-1.72(2H, m), 2.65-2.70(2H, m),3.73(3H, s), 3.89(3H, s), 5.04(2H, s), 6.10(1H, s), 6.78-6.79(1H, d),6.85-6.89(1H, m), 7.19-7.21(1H, m), 7.33-7.35(2H, m), 7.47-7.51(2H, m),7.64(1H, s).

Compound 35: δppm 1.00-1.25(3H, m), 1.69-1.72(2H, m), 2.36(3H, s),2.65-2.70(2H, m), 3.71(3H, s), 3.84(3H, s), 5.08(2H, s), 6.12(1H, s),6.75-6.78(1H, d), 7.21-7.26(1H, m), 7.33-7.38(3H, m), 7.50-7.53(1H, m),7.61(1H, s).

Compound 36: δppm 0.97(3H, t), 1.66(2H, m), 2.67(3H, s), 3.74(3H, s),3.89(3H, s), 5.04(2H, s), 6.78(1H, d), 6.85-6.88(1H, dd), 7.22(1H, m),7.33-7.35(2H, m), 7.46-7.49(2H, m), 7.64(1H, s).

Compound 37: δppm 1.05(3H, m), 1.57-1.64(2H, m), 2.16(3H, s),2.71-2.76(2H, t), 3.70(3H, s), 3.83(3H, s), 5.02(2H, s), 6.78(1H, d),6.87 (1H, m), 7.20(1H, m), 7.32(2H, m), 7.45(2H, m), 7.64(1H, s).

Compound 38: δppm(DMSO-d₆) 3.65(3H, s), 3.88(3H, s), 5.03(2H, s),-6.15(1H, s), 6.83-6.87(1H, dd), 6.91(1H, d), 7.09-7.17(2H, m),7.23-7.35(4H, m), 7.43-7.46(1H, m), 7.51-7.55(2H, m), 7.66(1H, s).

Compound 41: δppm 3.74(3H, s), 3.91(3H, s), 5.06(2H, s), 6.20(1H, s),6.86(2H, m), 7.22(2H, m), 7.33- 7.36 (2H, m), 7.56(3H, m), 7.66(1H, s),7.77(2H, d). Compound 50: δppm 2.34(3H, s), 3.74(3H, s), 3.89(3H, s),5.04(2H, s), 6.78-6.79(1H, d), 6.92-6.96(1H, dd), 7.18-7.21(1H, m),7.32-7.35(2H, m), 7.41-7.44(1H, d), 7.48-7.51(1H, m), 7.65(1H, s).

Compound 52: δppm 3.74(3H, s), 3.90(3H, s), 5.06(2H, s), 6.20(1H, s),6.80-6.86(1H, m), 7.18-7.22(1H, m), 7.32-7.37(4H, m), 7.41-7.44(2H, m),7.50-7.52(4H, m), 7.65(1H, s).

Compound 58: δppm 3.74(3H, s), 3.91(6H, d), 3.96(3H, s), 5.06(2H, s),6.19 (1H, s), 6.81-6.82(1H, m), .6.85 (1H, s), 6.93-7.04(3H, m),7.19-7.22(1H, m), 7.33-7.36(2H, m), 7.44-7.52(2H, m), 7.66(11H, s).

Compound 68: δppm(DMSO-d₆) 2.49(3H, s), 3.66(3H, s), 3.89(3H, s),3.92(2H, s), 5.00(2H, s), 6.78-6.79(1H, d), 6.85-6.89(1H, dd),7.10-7.22(6H, m), 7.26-7.29(2H, m), 7.42(1H, m), 7.61-7.66(2H, m).

Compound 100: 8ppm 2.54(3H, s), 3.87(3H, s), 4.04(3H, s), 5.02(2H, s),6.81-6.85(1H, s), 7.26(1H, d), 7.43-7.52(5H, m).

Compound 102: δppm 2.32(3H, s), 2.37(3H, s), 3.84(3H, s), 4.03(3H, s),5.05(2H, s), 6.13(1H, s), 6.76-6.79(1H, d), 7.26(1H, d), 7.34-7.43(3H,m), 7.45-7.46(1H, d).

Compound 103: δppm 2.18(3H, s), 2.37(3H, s), 3.91(3H, s), 3.98(3H, s),5.35(2H, s), 6.85(1H, s), 6. 86-6.88 (1H, d), 7.26-7.40(3H, m),7.49-7.52(1H, d), 7.62-7.65 (1H, d).

Compound 104: δppm 2.17(3H, s), 2.35(3H, s), 3.86(3H, s), 4.04(3H, s),5.00(2H, s), 6.78-6.85(2H, m), 7.20-7.25(1H, d), 7.40-7.61 (4H, m).

Compound 109: δppm 2.91-2.93(3H, d), 3.97(3H, s), 5.02(2H, s),6.23-6.26(1H, d), 6.82-6.86(3H, m), 7.20-7.23(1H, m), 7.34-7.37(1H, d),7.39-7.45(2H, m), 7.50-7.53(1H, m), 7.61-7.64(1H, d).

Compound 111: 8ppm 3.87(3H, s), 4.05(3H, s), 5.02(2H, s), 6.23-6.26(1H,d), 6.79-6.85(2H, m), 7.21(1H, d), 7.34-7.37(1H, d), 7.41-7.45(2H, m),7.47-7.53(1H, m), 7.61-7.64(1H, d).

Compound 401: δppm 1.32-1.36(6H, m), 2.39(3H, s), 3.27(1H, m), 3.74(3H,s), 3.89(3H, s), 5.03(2H, s), 6.72-6.73(1H, d), 6.83-6.87(1H, dd),7.17-7.20(1H, m), 7.31-7.34(2H, m), 7.46-7.52(2H, m), 7.63(1H, s).

Compound 402: δppm 0.93(3H, m), 1.45(4H, m), 2.35(3H, s), 2.60(2H, t),3.74(3H, s), 3.89(3H, s), 5.04(2H, s), 6.78(1H, d), 6.84-6.85 (1H, m),7.18-7.20(1H, m), 7.30-7.35(2H, m), 7.45-7.50(2H, d), 7.64(1H, s).

Compound 404: δppm 1.25(6H, m), 1.39(2H, m), 1.63(1H, m), 2.39(3H, s),2.62(2H, t), 3.72(3H, s), 3.86(3H, s), 5.01(2H, s), 6.78(1H, d), 6.84(1H, m), 7.20(1H, m), 7.32(2H, m), 7.45(2H, d), 7.64(1H, s).

Compound 405: δppm 0.88(3H, t), 1.42-1.52(8H, m), 2.38(3H, s), 2.64(2H,t), 3.72(3H, s), 3.86(3H, s), 5.01(2H, s), 6.78(1H, d), 6.84 (1H, m),7.20(1H, m), 7.32(2H, m), 7.45(2H, d), 7.64(1H, s).

Compound 408: 8ppm 2.37(3H, s), 3.2-3.6(1H, m), 3.72(3H, s), 3.85(3H,s), 5.09(2H, s), 6.18(1H, s), 6.76-6.79(1H, d), 7.18-7.21(1H, m),7.34-7.43(3H, m), 7.51-7.54(1H, m), 7.68(1H, 5).

Compound 409: δppm 0.96-1.03(6H, m), 1.58-1.63(4H, m), 2.71-2.79(4H, m),3.72(3H, s), 3.85(3H, s), 5.00(2H, s), 6.79(1H, d), 6.87 (1H, m),7.19(1H, m), 7.32(2H, m), 7.45(2H, m), 7.64(1H, s).

Compound 410: 8ppm 0.86-0.88(3H, m), 1.68-1.75(2H, m), 2.66-2.71(2H, m),3.87(3H, s), 4.05(3H, s), 5.02(2H, s), 6.80-6.92(3H, m), 7.21-7.26(1H,d), 7.39-7.69(3H, m).

Compound 411: δppm 3.87(3H, s), 4.05(3H, s), 5.02(2H, s), 6.73-6.77(1H,m), 6.87-6.88(1H, d), 6.97-7.00(1H, d), 7.21-7.24(1H, m), 7.28-7.32(2H,m), 7.42-7.57(6H, m).

Compound 412: δppm 0.94(3H, t), 1.46(2H, m), 2.35(3H, s), 2.60(2H, t),3.74(3H, s), 3.89(3H, s), 5.04(2H, s), 6.78(1H, d), 6.84 (1H, m),7.20(1H, m), 7.32(2H, m), 7.42-7.45(2H, d), 7.64(1H, s).

Compound 413: δppm 0.94(3H, m), 1.45(4H, m), 2.36(3H, s), 2.60(2H, t),3.86(3H, s), 4.05(3H, s), 5.00(2H, s), 6.78(1H, d), 6.84 (1H, m),7.20(1H, m), 7.38-7.45(4H, m).

Compound 414: δppm 0.88(3H, m), 1.48-1.65(8H, m), 2.36(3H, s), 2.62(2H,t), 3.86(3H, s), 4.05(3H, s), 5.00(2H,.s), 6.85(1H, m), 6.84 (1H, m),7.20(1H, m), 7.39-7.45(4H, m).

Formulation Example(Weight/Weight %)

Compound 6 60%  Sodium dodecylnaphthalenesulfate 2% Sodiumlignosulphonate 9% Kaolin complement to 100%

All the solid components are well mixed and shattered until the particlesize of the active ingredient reaches the standard in order to obtain60% wettable powder.

Example 6 35 % Emulsion Concentrate

Compound 1 35% Phosphorous acid 10% Ethylenoxy aliphatic acid glycerinester 15% Cyclohexanone complement to 100%

Phosphorous acid is dissolved in cyclohexanone, then the compound 1 andethylenoxy aliphatic acid glycerin ester are added, a emulsifiableconcentrate in transparent solution is obtained finally.

Example 7 30 % Aqueous Suspension Concentrate

Compound 25 30%  Sodium dodecylnaphthalenesulfate 4% Hemicellulose 2%Epoxypropane 8% Water complement to 100%

The mixture of compound 25, 80% of the amount of water should beingadded and sodium dodecylnaphthalenesulfate are shattered in a mill (1 mmball). Other components are dissolved in the rest water, and are addedunder stirring.

Example 8 25 % Suspension Emulsifier

Compound 12  25% Alkylsulphonates (emulsifier 1)   4% Ethylenoxyaliphatic acid glycerin ester   2% (emulsifier 2) Calciumdodecylbenzenesulfate (emulsifier 3) 1.5% Polyethylenoxyalkyl propylether (dispersant) 2.5% Cyclohexanone (solvent 1)  30% Petroleumfractions (boiling point >200° C.) complement to 100% (solvent 2)

Compound 12 is dissolved in 80% of the amount of solvent should beingadded, and then emulsifiers and dispersant are added, the mixture isstirred completely and shattered in a mill(1 mm ball). Other solventsare added.

Test of Biological Activity

Example 9 Fungicidal Activity Determination

Determination of fungicidal activities against plant diseases ofselected compounds were carried out by following procedure:

Plants were prepared in pot. Technical samples were dissolved in DMF anddiluted to required concentration by water. Test solution was sprayedonto potted plant. Pathogen inoculation was carried out after 24 hoursthen plants were hold in growth chambers containing constant temperatureand moisture for effect. When untreated plant was under desirabledisease severity (after 1 week approximately), assessment was carriedout by visual observation.

Part of test results:

At 200 ppm, compound 1, 2, 4, 5, 6,12,18,19, 25, 26, 33, 34, 35, 37, 50,52, 58, 69, 109, 402, 405, 409, 410, 413, 414 showed 100% controlagainst cucumber downy mildew, while compound 3, 24, 36, 38, 153, 411showed >95% control.

At 200 ppm, compound 2, 6, 18, 50, 58, 100, 402 showed 100% controlagainst cucumber grey mold, while 6, 101, 102, 103, 106, 412 showed >75%control.

At 200 ppm, compound 6, 7, 10 showed 100% against grape downy mildew,while 8, 106,154 showed >85% control.

At 200 ppm, compound 3, 101 showed >85% control against rice sheathblight.

At 200 ppm, compound 6, 8, 10 showed >85% control against rice blast.

At 200 ppm, compound 402, 412, 413 showed 100% control against wheatpowdery mildew, while 9, 101, 111, 410 showed >70% control.

At 200 ppm, compound 6 showed 100% control against wheat leaf rust,while 7, 10 showed >95% control and 8, 154 showed >75% control.

At 200 ppm, compound 6>90% and compound 7, 8, 9, 10, 11, 154 showed >80%control against wheat leaf blotch.

At 200 ppm, compound 6, 7 showed >100% control against tomato earlystage blight, while 8, 10 showed >90% control, while 11 showed >75%control.

At 200 ppm, compound 6 showed >95% control against tomato late blight,while 10 showed >75% control.

At 200 ppm, compound 5, 6 showed >95% control against corn leaf blight.Comparing with the compound JP51 in JP04-182461, the part of testresults of some compounds activity against cucumber downy mildew refersto table 3. TABLE 3 Comparision of fungicidal activity against cucumberdowny mildew (50 ppm) Compound 1 2 5 6 12 26 37 52 402 405 409 141 JP51control(%) 100 100 100 100 100 100 100 100 100 100 100 100 20

Example 10 Determination of Insecticidal/Acaricidal Activity

Numerous insect larvae were put into containers then were fed withtreated corn leaves. Potter's spraying tower was used as the sprayer andspraying volume was 1 mL. The spraying pressure was 13.5 lb/in².

Test Result:

At 10 ppm, compound 2, 5, 6 showed 100% control of culex mosquitoes. At600 ppm, compound 5 and 6 showed >50% control of army worm, diamondbackmoth and green peach aphid.

At 300 ppm, compound 7, 9, 10 showed 100% control of Mexican ladybeetle, while compound 7 showed >50% control of two-spotted spider mite.

1. A benzopyrone compounds, its features includes general formula (I):

wherein: A is selected from CH or N; B is selected from O, S or NR₉; R₉is selected from H or C₁-C₁₂alkyl; R₁ and R₂ are respectively selectedfrom H, C₁-C₁₂ alkyl or C₁-C₁₂ haloalkyl; R₃ is selected from H, C₁-C₁₂alkyl, C₁-C₁₂ haloalkyl or C₁-C₁₂ alkoxy; R₄, R₅, R₆, R₇, and R₈ may bethe same or different, selected from H, halo, CN, NO₂, C₁-C₁₂ alkyl,C₂-C₁₂ alkenyl, C₂-C₁₂ alkynyl, C₁-C₁₂ haloalkyl, C₁-C₁₂ alkoxy, C₁-C₁₂alkylthio, C₁-C₁₂ alkylsulfonyl, C₁-C₁₂ alkylcarbonyl, C₁-C₁₂alkoxyC₁-C₁₂alkyl, C₁-C₁₂ alkoxycarbonyl, C₁-C₁₂ alkoxycarbonyl C₁-C₁₂alkyl, C₁-C₁₂ haloalkoxyC₁-C₁₂ alkyl, or amino C₁-C,₂alkyl in whichamino is substituted with 0-2 C₁-C₁₂ alkyl, 0-3 substituted groups ofaryl, aryloxyl, arylC₁-C₁₂ alkyl, arylC₁-C₁₂ alkoxy, aryloxyC₁-C₁₂alkyl, arylC₁-C₁₂ alkoxylC₁-C₁₂ alkyl, heteroaryl, heteroarylC₁-C₁₂alkyl, or heteroarylC₁-C₁₂ alkoxyl, the 0-3 substituted groups may beselected from halo, NO₂, C₁-C₆ alkyl, C₁-C₆ haloalkyl, C₁-C₆ alkoxy orC₁-C₆ alkoxyC₁-C₆ alkyl, and the groups having general formula asfollows:

wherein: R₁₀ and R₁₁ are selected from H, C₁-C₁₂alkyl, aryl or arylC₁-C₁₂ alkyl; when R₃, R₄, R₅, R₆, R₇, and R₈ are all H, B is not NR₉;and its stereoisomer.
 2. The benzopyrone compound according to the claim1, characterized in that wherein general formula (I): A is selected fromCH or N; B is selected from O, S or NR₉; R₉ is selected from H or C₁-C₆alkyl; R₁ and R₂ are respectively selected from H, C₁-C₆ alkyl or C₁-C₆haloalkyl; R₃ is selected from H, C₁-C₆ alkyl, C₁-C₆ haloalkyl or C₁-C₆alkoxy; R₄, R₅, R₆, R₇, and R₈ may be the same or different, selectedfrom H, halo, CN, NO₂, C₁-C₆ alkyl, C₂-C₆ alkenyl, C₂-C₆ alkynyl, C₁-C₆haloalkyl, C₁-C₆ alkoxy, C₁-C₆ alkylthio, C₁-C₆ alkylsulfonyl, C₁-C₆alkylcarbonyl, C₁-C₆ alkoxyC₁-C₆ alkyl, C₁-C₆ alkoxycarbonyl, C₁-C₆alkoxycarbonylC₁-C₆ alkyl, C₁-C₆ haloalkoxyC₁-C₆ alkyl, or aminoC-C₆alkyl in which amino is substituted with 0-2 C₁-C₁₂ alkyl, 0-3substituted groups of aryl, aryloxyl, arylC₁-C₆ alkyl, arylC₁-C₆ alkoxy,aryloxyC₁-C₆ alkyl, arylC₁-C₆ alkoxylC₁-C₆ alkyl, heteroaryl,heteroarylC₁-C₆ alkyl, heteroarylC₁-C₆ alkoxyl, the 0-3 substitutedgroups may be selected from halo, NO₂, C₁-C₂ alkyl, C₁-C₂ haloalkyl,C₁-C₂ alkoxy or C₁-C₂ alkoxyC₁-C₂ alkyl, and groups having formula asfollows:

wherein: R₁₀ and R₁₁ are respectively selected from H, C₁-C₆ alkyl, arylor arylC₁-C₆ alkyl; when R₃, R₄, R₅, R₆, R₇, R₈ are all H, B is not NR₉.3. The benzopyrone compound according to the claim 2, characterized inthat wherein general formula (I): A is selected from CH or N; B isselected from O or NH; R₁ and R₂ are respectively selected from methyl;R₃ is selected from H or methyl; R₄, R₅, R₆, R₇, and R₈ may be the sameor different, respectively selected from H, halo, CN, NO₂, C₁-C₆ alkyl,C₂-C₆ alkenyl, C₁-C₆ haloalkyl, C₁-C₆ alkoxy, C₁-C₆ alkylcarbonyl, C₁-C₆alkoxyC₁-C₆ alkyl, C₁-C₆alkoxycarbonyl, C₁-C₆ alkoxycarbonylC₁-C₃alkyl,C₁-C₃ haloalkoxyC₁-C₃ alkyl, or amino C₁-C₃alkyl in which amino issubstituted with 0-2 C₁-C₃ alkyl, phenyl, phenoxy, phenyl C₁-C₂ alkyl,phenylC₁-C₂ alkoxy, phenoxy C₁-C₂ alkyl, phenylmethyl, phenylmethoxyl,or phenylmethoxy C₁-C₂ alkyl substituted with 0-2 halo, NO₂, C₁-C₂alkyl, C₁-C₂ haloalkyl, C₁-C₂ alkoxy or C₁-C₂ alkoxyC₁-C₂ alkyl, and thesubstituted group having general formula as follows:

wherein: R₁₀ and R₁₁ are respectively selected from H or C₁-C₆ alkyl;when R₃, R₄, R₅, R₆, R₇, and R₈ are all H, B is not NH.
 4. Thebenzopyrone compound according to the claim 3, characterized in thatwherein general formula (I): A is selected from CH or N; B is selectedfrom O or NH; R₁ and R₂ are selected from methyl; R₃ is selected from Hor methyl; R₄, R₅, R₆, R₇, and R₈ may be the same or different,respectively selected from H, Cl, Br, F, CN, C₁-C₆ alkyl, C₁-C₆haloalkyl, C₁-C₆ alkylcarbonyl, C₁-C₆ alkoxy, C₁-C₆ alkoxyC₁-C₃ alkyl,C₁-C₃ haloalkoxyC₁-C₃ alkyl, amino C₁-C₃alkyl in which amino issubstituted with 0-2 C₁-C₃ alkyl, phenyl, phenoxy, phenylmethyl,phenylmethoxyl, substituted with 0-2 halo, NO₂, C₁-C₂ alkyl, C₁-C₂haloalkyl, C₁-C₂ alkoxy or C₁-C₂ alkoxyC₁-C₂ alkyl, and the substitutedgroups having general formula as follows:

wherein: R₁₀ and R₁₁ are selected from methyl; when R₃, R₄, R₅, R₆, R₇,R₈ are all H, B is not NH.
 5. A preparation method of benzopyronecompounds, characterized in that: The compound of general formula (I) isprepared by reaction of Benzylhalide having general formula (II) with7-OH-benzopyrone compounds having general formula (HI) at the present ofbase:

wherein: Z is leaving group selected from Cl or Br; A is selected fromCH or N; B is selected from O, S or NR₉; R₉ is selected from H or C₁-C₁₂alkyl; R₁ and R₂ are respectively selected from H, C₁-C₁₂ alkyl orC₁-C₁₂ haloalkyl; R₃ is selected from H, C₁-C₁₂ alkyl, C₁-C₁₂ haloalkylor C₁-C₁₂ alkoxy; R₄, R₅, R₆, R₇, and R₈ may be the same or different,respectively selected from H, halo, CN, NO₂, C₁-C₁₂ alkyl, C₂-C₁₂alkenyl, C₂-C₁₂ alkynyl, C₁-C₁₂ haloalkyl, C₁-C₁₂ alkoxy, C₁-C,₂alkylthio, C₁-C₁₂ alkylsulfonyl, C₁-C₁₂ alkylcarbonyl, C₁-C₁₂alkoxyC₁-C₁₂alkyl, C₁-C₁₂ alkoxycarbonyl, C₁-C₁₂ alkoxycarbonylC₁-C₁₂alkyl, C₁-C₁₂ haloalkoxyC₁-C₁₂ alkyl, or amino C₁-C₁₂alkyl in whichamino is substituted with 0-2 C-C₁₂ alkyl; 0-3 substituted groups ofaryl, aryloxyl, arylC₁-C₁₂ alkyl, arylC₁-C₁₂ alkoxy, aryloxy C₁-C₁₂alkyl, arylC₁-C₁₂ alkoxylC₁-C₁₂ alkyl, heteroaryl, heteroarylC₁-C₁₂alkyl, or heteroaryl C₁-C₁₂alkoxyl, the 0-3 substituted groups may beselected from halo, NO₂, C₁-C₆ alkyl, C₁-C₆ haloalkyl, C₁-C₆alkoxy orC₁-C₆ alkoxyC₁-C₆ alkyl, and the groups having general formula asfollows:

wherein: R₁₀ and R₁₁ are selected from H, C₁-C₁₂ alkyl, aryl or arylC₁-C₁₂ alkyl; when R₃, R₄, R₅, R₆, R₇, and R₈ are all H, B is not NR₉.6. According to the claim 1, application of the benzopyrone compoundsfor controlling insects in plants.
 7. According to the claim 1,application of the benzopyrone compounds for controlling fungi inplants.
 8. A composition of fungicides and insecticides comprises thecompound of the claim 1 as an active ingredient, wherein the weightpercentage of the active ingredient in the composition is from 0.1% to99%.